Add the potatoes to a medium stockpot. Cover with cold water and bring the water to a boil over high heat. Reduce the heat to medium and simmer until tender and easily pierced with a fork, about 30 minutes.
Drain the potatoes and return them back to the pot for just a minute so that any remaining water is cooked off. Add to the bowl of a stand mixer fitted with the whisk attachment.
Heat the cream in a small saucepan over low heat and bring to a simmer. Whisk the potatoes on low speed until mashed, then alternate adding the cream and the butter, until they are fully incorporated.
Add the cheddar cheese and continue to whisk until the cheese has completely melted into the potatoes. Season with salt and pepper and serve in a medium serving bowl.